EP2262788B1 - Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen - Google Patents

Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen Download PDF

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EP2262788B1
EP2262788B1 EP09714427.3A EP09714427A EP2262788B1 EP 2262788 B1 EP2262788 B1 EP 2262788B1 EP 09714427 A EP09714427 A EP 09714427A EP 2262788 B1 EP2262788 B1 EP 2262788B1
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Prior art keywords
membrane
catalyst
products
process according
polymeric
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German (de)
English (en)
French (fr)
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EP2262788A1 (de
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Stefan Birnbach
Hans Klink
Hans-Martin Mugrauer
Hartwig Voss
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C07D317/38—Ethylene carbonate

Definitions

  • the present invention relates to a process for the continuous production of a 1,3-dioxolan-2-one, in which a discharge from the reaction zone is subjected to a separation by means of a semipermeable membrane for the separation of polymeric by-products.
  • 1,3-dioxolan-2-ones such as ethylene carbonate or propylene carbonate
  • a corresponding oxirane such as ethylene oxide or propylene oxide
  • carbon dioxide in the liquid phase
  • a catalyst homogeneously present in the liquid phase.
  • the workup of the reaction ie the isolation of the product and the separation of the catalyst for recycling in the reaction zone is carried out by known methods, such as distillation, extraction or stripping.
  • a common procedure involves the separation by distillation of low boilers and product and the subsequent recycling of the catalyst-containing bottoms product into the reaction.
  • a disadvantage of this procedure is that high-boiling by-products of the reaction, such as the resulting from the oxiranes cyclic and linear polyether aufpegeln in the reaction system.
  • These high boilers which may have molecular weights up to about 20,000 daltons, result in an increasing viscosity in the catalyst recycle stream.
  • z. B. in the distillative workup of enriched high boilers distillation bottoms are discharged together with the catalyst contained therein. This leads to an economic disadvantage of the process by the necessary shutdown of the plant and the costs incurred in the high boiler disposal catalyst and product loss.
  • KR 2007 016 666 describes a continuous catalytic process for the preparation of alkylene carbonates from alkylene oxides and CO2 and separation of the product mixture by means of membrane separation processes.
  • the molecular weight of the polymeric by-products contained in the discharge from the reaction zone initially increases at the beginning of the process according to the invention until the separation limit of the membrane (s) used is reached. Thereafter, due to the discharge of the high molecular weight fraction essentially a stationary state, that is, the concentration of polymeric by-products in the discharge from the reaction zone increases substantially no longer.
  • the "high molecular weight fraction" of the polymeric by-products is within the scope of the invention that portion which is retained by the membrane.
  • the "low molecular weight fraction" of the polymeric by-products is that which is capable of passing through the membrane in to convert the permeate (ie the separation limit of the membrane used determines what in the context of the invention, the low molecular weight and what is the high molecular weight fraction of the polymeric by-products). From the recycled with the catalyst in the low molecular weight fraction formed by further addition of oxirane again higher molecular weight by-products.
  • the reaction of the oxirane (II) with carbon dioxide in step a) takes place in a reaction zone which may have one or more (eg two, three or more than three) reactors.
  • the reactors may be the same or different reactors. These can be z. B. each have the same or different mixing characteristics and / or be subdivided by internals one or more times.
  • Suitable pressure-resistant reactors for the preparation of the 1,3-dioxolan-2-ones of the formula I are known to the person skilled in the art. These include the commonly used reactors for gas-liquid reactions, such as. B. tube reactors, tube bundle reactors, gas circulation reactors, bubble columns, loop apparatus, stirred tank (which can also be designed as stirred tank cascades), air-lift reactors, etc.
  • the temperature in the reaction in step a) is generally about 60 to 160 ° C, preferably 70 to 150 ° C, particularly preferably 90 to 145 ° C.
  • a different temperature can be set in each downstream reactor than in the previous reactor.
  • the respectively downstream reactor is operated at a higher temperature than the preceding reactor.
  • each reactor may have two or more reaction zones operating at different temperatures. For example, in a second reaction zone another, preferably a higher temperature than in the first reaction zone or in each subsequent reaction zone, a higher temperature than in a previous one Reaction zone can be adjusted, for. B. to achieve the fullest possible sales.
  • the reaction pressure in step a) is generally about 2 to 50 bar, particularly preferably 5 to 40 bar, in particular 10 to 30 bar. If desired, when using a plurality of reactors in each subsequent reactor, a different (preferably higher) pressure can be set than in the previous reactor.
  • the starting materials carbon dioxide and oxirane can be conducted in the reaction zone in cocurrent or in countercurrent. Also possible is an embodiment in which carbon dioxide and oxirane are passed in one part of the reaction zone in direct current and in another part in countercurrent. Preferably, carbon dioxide and oxirane are passed in countercurrent throughout the reaction zone.
  • a liquid discharge is removed according to the invention and used for the following work-up.
  • a gaseous discharge can be removed at the top of the reactor or, in a reaction zone of several reactors.
  • the gaseous discharge can be partially or completely returned to the reaction zone.
  • the gaseous discharge can also be partially or completely discharged, in order to avoid a Aufpegeln inert gaseous components in the reaction zone.
  • Suitable onium salts are in principle all compounds of this type, including in particular ammonium, phosphonium and sulfonium salts of the general formula IIIa to IIIc in which the substituents R are the same or different hydrocarbon radical having in each case 1 to 20 C atoms, the sum of the C atoms in the radicals R each not greater than 24, and in which X- is an anion equivalent, preferably halide, especially bromide or iodide.
  • ammonium salts of the formula IIIa in particular tetraethylammonium bromide.
  • those compounds IIIa are preferred in which three of the radicals R are C 1 -C 4 -alkyl groups, such as methyl or ethyl, and the fourth radical R is benzyl or unbranched C 6 - to C 18 -alkyl.
  • Phosphonium salts IIIb which are derived from triphenylphosphine and whose fourth substituent has been introduced into the molecule by quaternization with a C 1 to C 6 -alkyl bromide are also preferred as catalyst.
  • a suitable sulfonium salt IIIc is, for example, the easily prepared trimethylsulfonium iodide.
  • the ammonium and phosphonium salts are more suitable than the sulfonium salts.
  • the hydrocarbon radicals R in the compounds IIIa to IIIc may be branched or preferably unbranched C 1 to C 20 alkyl groups, arylalkyl groups such as the benzyl groups, the cyclohexyl group and aromatic groups such as the phenyl or the p-tolyl group. Further, alkyl radicals R may also be linked together, such as to form a piperidine ring. As anions other than halide, for example, sulfate and nitrate into consideration.
  • Suitable metal salts are salts of alkali metals, alkaline earth metals and transition metals, in particular divalent transition metals, for example, sodium, potassium, magnesium, calcium, aluminum, manganese (II), iron (II), nickel (II ), Copper (II), zinc, cadmium or lead (II) salts.
  • Suitable anions for these salts are sulfate, nitrate, phosphate, carbonate, acetate, formate and especially halides such as chloride, bromide and iodide.
  • zinc salts such as zinc sulfate, zinc nitrate, zinc phosphate, zinc carbonate, zinc acetate, zinc formate, zinc chloride, zinc bromide or zinc iodide. It is of course also possible to use mixtures of such metal salts, the same also applies to the above-mentioned onium salts. Mixtures of onium salts with metal salts are possible and show in some cases surprising advantages.
  • the amount of onium salts and / or metal salts used as catalysts is generally not critical. About 0.01 to 3 wt .-%, based on the oxirane (II) used, are preferably used.
  • the catalysts used are alkali metal bromides, alkali metal iodides, tetraalkylammonium bromides, tetraalkylammonium iodides, halides of divalent metals or mixtures thereof.
  • the catalysts used are a mixture of onium salts, in particular ammonium, phosphonium and / or sulfonium salts of the general formula IIIa to IIIc, and zinc salts, in particular those explicitly mentioned above.
  • the effective amounts of the zinc salts are between 0.1 and 1.0 mol, preferably between 0.3 and 0.7 mol, per mole of the onium salt.
  • suitable inert solvents are, for. As dioxane, toluene or acetone. If a solvent is used for the reaction, it is normally used in amounts of about 10 to 100% by weight, based on the oxirane (II) used. If the process product I is liquid under the reaction conditions, it is expedient to use this as solvent, preferably as the sole solvent. It has proven to be advantageous in such cases to dissolve the catalyst in the process product and to meter in this solution, virtually no further solvents are added in the reaction reactor.
  • the concentration of the catalyst in the process product (I) I is usually 0.5 to 20 wt .-%, in particular 1 to 15 wt .-%.
  • the molar ratio of educt amount (II) added in the same time unit to the process product (I) added with the catalyst is generally from 100: 1 to 1: 1, in particular from 50: 1 to 2: 1.
  • the educt streams of oxirane (II) and carbon dioxide are preferably used in a molar ratio of 1: 1 to 1: 1.05, in particular 1: 1 to 1: 1.02.
  • a possible slight excess of carbon dioxide is advantageous in order to compensate for the losses of carbon dioxide while relaxing the discharge from the reaction zone.
  • the method according to the invention achieves virtually quantitative conversions of (II), generally at least 99%, in particular at least 99.5%, especially at least 99.9%.
  • R 1 other than hydrogen may bear one or more substituents, such as halogen, nitro groups, free or substituted amino groups, hydroxyl groups, formyl groups or cyano groups or contain ether, ketone or ester groups.
  • R 1 is hydrogen.
  • the radicals R 2 and R 3 is typically hydrogen or the methyl group as well as those groups which are joined together to form a five- or six-membered ring, for which is cyclohexene oxide as an example Compound II. If II contains two oxirane rings each having a (CH 2 -) group, the corresponding bis-dioxolanes I are contained; Oxirane rings, which are substituted on both carbon atoms, are usually attacked more slowly than those substituted on only one of the carbon atoms. As oxirane (II), preference is given to using ethylene oxide or propylene oxide, especially ethylene oxide.
  • the process according to the invention is used to prepare ethylene carbonate or propylene carbonate.
  • the work-up in step b) comprises, as an essential step, a membrane separation process.
  • a membrane separation process it is possible in an advantageous manner to separate the catalyst used for the reaction and the high boilers formed in the reaction so far that a catalyst-poor or ideally catalyst-free Hochsiederausschleusung is possible.
  • the permeate in a multi-stage membrane separation based on all stages at least 70 wt .-%, preferably at least 80 wt .-%, in particular at least 90 wt .-%, of the catalyst contained in the current used for membrane separation.
  • the discharge from the reaction zone contains a proportion of polymeric by-products of at most 6 wt .-%, more preferably at most 5 wt .-%, in particular at most 4 wt .-%, based on the total weight of the reaction.
  • the liquid separation from the reaction zone is not used directly for the membrane separation in step b), but instead first subjected to a separation of a portion of the components contained therein.
  • a stream consisting essentially of compound (I), the catalyst and the polymeric by-products is separated from the discharge from the reaction zone.
  • this current is then at least partially subjected to separation by means of a semipermeable membrane.
  • this stream is divided into a first and a second partial stream, wherein the first partial stream is returned to the reaction zone and the second partial stream is subjected to separation by means of a semipermeable membrane.
  • carbon dioxide and / or oxirane of the formula II dissolved therein are at least partially separated from the discharge from the reaction zone prior to the membrane separation.
  • a stream is separated from the discharge from the reaction zone before the membrane separation, which consists essentially of the reaction product, d. H. the compound (I) consists.
  • the separation of carbon dioxide and / or oxirane can be effected via a separate gaseous discharge from the reaction zone.
  • the discharge from the reaction zone to separate off the carbon dioxide and / or oxirane (II) dissolved therein can first be subjected to a relaxation step.
  • a gas phase which is generally carried out consists essentially of carbon dioxide and / or oxirane (II).
  • the gas phase resulting in the relaxation step may be partially or completely recycled to the reaction zone. This return can be carried out together with one of the gas streams fed into the reaction zone or separately.
  • the liquid phase obtained in the relaxation step is preferably subjected to a further separation according to a customary method known to the person skilled in the art.
  • the liquid phase is subjected to distillation to obtain a stream consisting essentially of the compound (I) and a stream consisting essentially of the compound (I), the catalyst and the polymeric by-products. The latter stream can then be used for membrane separation.
  • this stream contains a proportion of high-boiling by-products of at most 30 wt .-%, preferably at most 25 wt .-%, particularly preferably at most 20 wt .-%, based on the total weight of the compound (I), the catalyst and the polymeric by-products of existing stream.
  • the latter stream is separated into a first and a second partial stream, wherein the first partial stream is returned to the reaction zone and the second partial stream is used for membrane separation.
  • distillative separation of the reaction can be carried out by conventional methods known in the art.
  • Suitable apparatus for the separation by distillation include distillation columns, such as tray columns, which may be provided with bells, sieve plates, sieve trays, packages, internals, valves, side draws, etc.
  • Particularly suitable partition wall columns which can be provided with 39abmann, returns, etc.
  • evaporators such as thin film evaporators, falling film evaporators, Sambay evaporators, etc., and combinations thereof.
  • the distillation is preferably carried out at a bottom temperature in the range of about 30 to 160 ° C, particularly preferably 50 to 150 ° C, in particular 70 to 140 ° C.
  • the distillation may be carried out under normal pressure, elevated pressure or reduced pressure.
  • the pressure in the distillation is preferably in a range from about 0.0005 bar to 1.5 bar, more preferably 0.001 bar to 1.2 bar, in particular 0.01 bar to 1.1 bar.
  • the retentate obtained is a concentrated solution of the high molecular weight fraction of the polymeric by-products (high-boiling impurities) which has been depleted of catalyst.
  • the separation by means of the membrane in step b) takes place in two or more than two stages (eg in 3, 4, 5 or 6).
  • the amount of permeate separated off during the membrane separation is at least partially supplemented in the retentate by the addition of liquid.
  • This supplement can be continuous or discontinuous.
  • a membrane separation (ultrafiltration), in which the retained material is not concentrated, but in which the separated amount of permeate is supplemented, is also referred to as diafiltration. If the separation by membrane in step b) takes place in two or more than two stages, one stage, a part of the stages or all stages can be configured as diafiltration. If the product (I) is used as the solvent for the reaction, it is also preferable to use the compound (I) as the additionally supplied liquid in the diafiltration.
  • the amount of liquid separated with the permeate is not supplemented.
  • concentration An ultrafiltration in which the separated amount of permeate is not supplemented. If the separation by means of the membrane in step b) takes place in two or more than two stages, then one of the stages, a part of the stages or all stages can be configured as a concentration.
  • the membrane separation comprises a plurality of stages connected in series.
  • the feed stream is fed to a first membrane separation (first stage), with the resulting retentate stream being returned to the subsequent stage.
  • the retentate stream taken from the last stage is finally subjected to a workup to obtain a discharge stream containing the high molecular weight fractions of the polymeric by-products and a stream enriched in compound (I) and / or solvent.
  • the separation by means of membrane in step b) first comprises at least one concentration step and then at least one diafiltration step.
  • step b) preferably takes place continuously.
  • Suitable semipermeable membranes have sufficient permeability to the catalyst present homogeneously in the reaction medium. They also have a sufficient retention capacity for the high molecular weight fraction of the polymeric by-products contained in the reaction medium, d. H. they are capable of higher molecular weight compounds, which are z. B. by oligomerization or polymerization of the oxiranes (II), retain.
  • the mean average pore size of the membrane is generally 0.8 to 20 nm, preferably 0.9 to 10 nm, particularly preferably 1 to 5 nm.
  • the semipermeable membranes used according to the invention have at least one separating layer, which may consist of one or more materials. These materials are preferably selected from organic polymers, ceramics, metals, carbon, and combinations thereof. Suitable materials are stable at the filtration temperature in the feed medium. Preferred are membranes of at least one inorganic material.
  • Suitable ceramic materials are, for example, ⁇ -alumina, zirconium oxide, titanium dioxide, silicon carbide or mixed ceramic materials.
  • Suitable organic polymers are, for. As polypropylenes, polytetrafluoroethylenes, polyvinylidene difluorides, polysulfones, polyethersulfones, polyether ketones, polyamides, polyimides, polyacrylonitriles, regenerated cellulose, silicone polymers.
  • an inorganic membrane composed of several layers.
  • the separating layers are usually applied to a single or multilayer porous substructure of the same or even several different materials as the separating layer.
  • Examples of possible material combinations are listed in the following table: Interface Substructure (coarser than separation layer) metal metal ceramics Metal, ceramic or carbon polymer Polymer, metal, ceramic or ceramic on metal carbon Carbon, metal or ceramic Ceramics: z. As ⁇ -Al 2 O 3 , ZrO 2 , TiO 2 , SiC, mixed ceramic materials Polymer: z.
  • PP PTFE, PVDF, polysulfone, polyethersulfone, polyetheretherketone, polyamide, polyacrylonitrile, regenerated cellulose
  • the membranes can in principle be used in flat, tubular, multi-channel element, capillary or winding geometry, for the corresponding pressure housing, which allow a separation between retentate and the permeate, are available.
  • the optimal transmembrane pressures between retentate and permeate are dependent on the diameter of the membrane pores, the hydrodynamic conditions that influence the top layer structure, and the mechanical stability of the membrane at the filtration temperature. They are generally in a range of 0.2 to 30 bar, more preferably in a range of 0.5 to 20 bar. Higher transmembrane pressures usually lead to higher permeate fluxes. In this case, in the case where several modules are connected in series, the transmembrane pressure for each module can be lowered by increasing the permeate pressure and thus adjusted.
  • the operating temperature depends on the membrane stability and the temperature stability of the feed.
  • a suitable temperature range for the membrane separation in step b) is 20 to 90 ° C, preferably 40 to 80 ° C.
  • the melting points of the products can limit the temperature range. Higher temperatures usually lead to higher permeate flows.
  • the achievable permeate fluxes are highly dependent on the type of membrane used and membrane geometry, on the process conditions, on the feed composition (essentially the polymer concentration).
  • the flows are typically in a range of 0.5 to 100 kg / m 2 / h, preferably 1 to 50 kg / m 2 / h.
  • the following membranes are z. B. applicable: Manufacturer membrane Separation limit (kD) pore diameter (nm) Inopor GmbH ⁇ -Al 2 O 3 on ceramic / 1, 2 5 nm; 7.5 kD TiO 2 on ceramic / 1, 2 5 nm; 8.5 kD TiO 2 on ceramic / 1, 2 0.9 nm; 0.5 kD TiO 2 on ceramic / 1, 2 1 nm; 0.8 kD ZrO 2 on ceramic / 1, 2 3 nm; 2 kD Atech innovations GmbH UF / TiO 2 on ⁇ -Al 2 O 3/1, 2 5, 10 and 20 kD Rhodia / Orelis UF / ZrO 2 or TiO 2 on ceramic / 1,2 15 kD Pall Schumacher UF / TiO 2 or ZrO 2 on ceramic / 1,2 5 and 10 nm Creavis UF / ZrO 2 on ⁇ -Al 2 O 3 and metal / 3 25 nm 1: tube
  • the membrane separation in step b) can also be carried out discontinuously in otherwise continuous reaction, for example by repeated passage through the membrane modules.
  • the membrane separation in step b) is carried out continuously, for example by a single pass through one or more successively connected membrane separation stages.
  • the high-boiling impurities can be separated by methods known per se.
  • the retentate is subjected to distillation to yield a high-boiling-point enriched effluent stream and one stream enriched in compound (I).
  • the distillation can be carried out with known per se apparatuses, for. B. by using at least one short-path evaporator.
  • Fig. 1 represents a scheme of suitable for carrying out the process of the invention system, which has been omitted for the sake of clarity on the reproduction of such details, which are not relevant to the explanation of the invention.
  • the plant comprises a reaction zone (1) comprising at least one reactor. Via the pipeline (2), an oxirane (such as ethylene oxide) is introduced into the reaction zone (1) and CO 2 is introduced into the reaction zone (1) via the pipeline (3). A discharge (4) is taken from the reactor (1) via the pipeline leaving the reaction zone (1) and fed to the work-up stage (5).
  • an oxirane such as ethylene oxide
  • the discharge (4) is first fed to a flash vessel (not shown), wherein a phase separation into a carbon dioxide-containing gas phase and a liquid phase takes place, which is then fed to a further work-up in the work-up stage (5).
  • the gas phase obtained during the expansion may additionally contain amounts of unreacted oxirane.
  • a distillative separation is carried out to obtain a gas phase (6) which consists of the low-boiling components of the reaction effluent (ie essentially of carbon dioxide and / or oxirane), essentially of the 1,3-dioxolane-2 stream (7) and a bottom product (8) consisting essentially of the 1,3-dioxolan-2-one, the catalyst and the polymeric by-products of the reaction.
  • the stream (8) containing the catalyst and the polymeric by-products is divided into a first part-stream (8a) which is returned to the reaction zone (1) and a second part-stream (8b) which is fed to the membrane separation (9).
  • the membrane separation (9) can be carried out in one or more stages.
  • a retentate stream (10) is obtained which contains the high boiler components of the reactor discharge retained by the semipermeable membrane as well as oxirane and optionally small amounts of catalyst not separated off.
  • This retentate stream (10) is fed to a work-up stage (11), which in a specific embodiment is designed as a short-path evaporator.
  • the high boiler stream (12) obtained in the work-up stage (11) is discharged from the process.
  • the likewise obtained 1,3-dioxolan-2-one enriched stream (13) is again fed to the membrane separation (9).
  • the permeate (14) obtained in the membrane separation (9), consisting essentially of the 1,3-dioxolan-2-one, the catalyst and the proportions of high boilers which were not retained in the membrane separation (9), is described in US Pat a first embodiment in the work-up stage (5) attributed.
  • the permeate stream (14) is recycled to the reaction zone (1). If necessary, fresh catalyst can be fed into the reaction zone (1) via the feed stream (15).
  • Catalyst-containing reactor effluents from the ethylene carbonate synthesis (catalyst: bromide salt mixture) were used, which were freed from low-boiling distillates and from which ethylene carbonate was partly removed by distillation.
  • This ethylene carbonate, catalyst and polymer-containing feed was worked up in batches in all experiments.
  • the material used was brought from a circulation vessel with a pump to a pressure of 15 bar and passed through the membrane tubes at a temperature of 70 ° C and a speed of 2 m / s, then relaxed again to normal pressure and fed back into the circulation vessel.
  • At atmospheric pressure separated permeate was collected for permeate flow determination in a vessel on a balance and continuously replaced by an equal amount of Diafiltriermedium (in all experiments ethylene carbonate).
  • the diafiltration was usually carried out with a solvent exchange coefficient MA of about 3. D. h.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Epoxy Compounds (AREA)
  • Polyethers (AREA)
EP09714427.3A 2008-02-29 2009-02-27 Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen Not-in-force EP2262788B1 (de)

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EP09714427.3A EP2262788B1 (de) 2008-02-29 2009-02-27 Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen

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EP08152146 2008-02-29
PCT/EP2009/052354 WO2009106605A1 (de) 2008-02-29 2009-02-27 Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen
EP09714427.3A EP2262788B1 (de) 2008-02-29 2009-02-27 Membrantrennverfahren zur hochsiederabtrennung bei der herstellung von 1,3-dioxolan-2-onen

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EP2262788A1 EP2262788A1 (de) 2010-12-22
EP2262788B1 true EP2262788B1 (de) 2016-02-24

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US (1) US20110009645A1 (es)
EP (1) EP2262788B1 (es)
JP (1) JP5787523B2 (es)
KR (1) KR20100124769A (es)
CN (1) CN101965340B (es)
BR (1) BRPI0907545A2 (es)
CA (1) CA2715313C (es)
EA (1) EA201001325A1 (es)
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EP4378934A1 (en) * 2021-07-26 2024-06-05 Sumitomo Seika Chemicals Co., Ltd. Recovery method and production method for cyclic carbonate
EP4303255A1 (de) * 2022-07-07 2024-01-10 RAMPF Eco Solutions GmbH & Co. KG Aufarbeitung von kunststoffsolvolysegemischen

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JP4624056B2 (ja) * 2004-10-04 2011-02-02 旭化成ケミカルズ株式会社 アルキレンカーボネートの連続的製造方法
JP4673028B2 (ja) * 2004-10-04 2011-04-20 旭化成ケミカルズ株式会社 エチレンカーボネートの精製方法
KR20070016666A (ko) * 2005-08-04 2007-02-08 최영철 고순도 알킬렌카보네이트를 합성하기 위한 막분리기를이용한 촉매부가반응공법.
SG147866A1 (en) * 2006-05-23 2008-12-31 Basf Se Method for producing polyether polyols
JP4890611B2 (ja) * 2006-06-13 2012-03-07 ビーエーエスエフ ソシエタス・ヨーロピア 複合膜の製造方法
WO2008043790A2 (de) * 2006-10-11 2008-04-17 Basf Se Verfahren zur herstellung oberflächenmodifizierter nanopartikulärer metalloxide, metallhydroxide und/oder metalloxidhydroxide
BRPI0809159B1 (pt) * 2007-03-23 2016-06-07 Basf Se processo para produzir partículas nanoparticuladas modificadas na superfície, uso de partículas nanoparticuladas modificadas na superfície, processo para produzir uma suspensão aquosa de partículas nanoparticuladas modificadas na superfície, suspensões aquosas, e, uso das mesmas
PT2155386E (pt) * 2007-05-10 2012-04-16 Basf Se Processo para a produção de aminas

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Publication number Publication date
EP2262788A1 (de) 2010-12-22
US20110009645A1 (en) 2011-01-13
BRPI0907545A2 (pt) 2015-07-28
JP2011513281A (ja) 2011-04-28
ES2566544T3 (es) 2016-04-13
CA2715313A1 (en) 2009-09-03
EA201001325A1 (ru) 2011-02-28
KR20100124769A (ko) 2010-11-29
CN101965340B (zh) 2014-09-17
WO2009106605A1 (de) 2009-09-03
CN101965340A (zh) 2011-02-02
TW200942321A (en) 2009-10-16
JP5787523B2 (ja) 2015-09-30
CA2715313C (en) 2016-08-02
MX2010008738A (es) 2010-08-31

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